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Ok I already pretty much know the answer is NO WAY but will ask anyway. I have a 04 2.4 FWD highlander with 37K miles on it. I just came across a really great deal on a 30ft speedboat with outboards that weighs in at 3800lbs. With Gas in it and the trailer I imagine it would be around 4300lbs. Is there any modifications I can make to the transmission or engine or car in general to pull this kind of weight? Pretty sure the 2.4 wont have enough to pull that kind of weight out of the water.

Otherwise my best choice is find a old F-150 I guess.
 

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2005 HL Ltd. 4WD V6
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oh no!

Short of dropping in a smalll block Chevy, DON'T DO IT. You know darn well you shouldn't, as you admitted it! You're asking for it, so why try it? If you get into an accident, which is a real good possibility, your insurance company just might decline to help you and you might even get a citation from the cops. Don't kill the HL, get the F150.
 

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The 4 cyl Highlander is rated 3,000 lbs. maximum (brochure) for towing with the tow package. The 6 cyl is rated for 3,500 lbs. with the tow package. Even if the 4 cyl was rated for your weight, the Highlander would need the tow package consisting of the following(from brochure):

Upgraded radiator, tranny oil cooler, 130 amp alternator, engine oil cooler, power steering oil cooler, and 120 watt fan coupling
 
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